Chicago Briefs @chicagobriefs.bsky.social · 09/05/2026Underwear that matches the marine layers at sunrise #bikinibriefs #calzones #mutande #slips 🩲: N2N Bodywear 151
Chicago Briefs @chicagobriefs.bsky.social · 12/04/2026These skies over Lake Michigan can’t be beat #thong #manthong #tanga #string 161
Chicago Briefs @chicagobriefs.bsky.social · 11/04/2026Inside vs out 🩲: Box Menswear #thong #tanga #manthong #string 151
Chicago Briefs @chicagobriefs.bsky.social · 09/04/2026“Boxing” at the gym 🥊 🩲: Box Menswear #tanga #manthong #thong 171
Chicago Briefs @chicagobriefs.bsky.social · 08/04/2026Chicago Riverwalk briefing 🩲: Intimissimi Uomo 131
Chicago Briefs @chicagobriefs.bsky.social · 25/03/2026@petitqunderwear.bsky.social thong for me this morning 272
Chicago Briefs @chicagobriefs.bsky.social · 12/01/2026🌴🌴🌴🌴💪🏻💪🏻💪🏻💪🏻 🩲: @petitqunderwear.bsky.social 1102
Chicago Briefs @chicagobriefs.bsky.social · 08/12/2025Orange’nt you glad it’s Monday? 👖: DSG 🩲: Dietz 131
Chicago Briefs @chicagobriefs.bsky.social · 04/12/2025Gym to the streets in yellow 💛 👖: Nike 🩲: Dietz 131
Chicago Briefs @chicagobriefs.bsky.social · 07/09/2025Pushing though the cool autumn weather 🍂 👖: Nike 🩲: GX3 121
Chicago Briefs @chicagobriefs.bsky.social · 03/09/2025Late summer Chicago mornings ☀️ 👖: Nike 🩲: Bikkembergs 362
Chicago Briefs @chicagobriefs.bsky.social · 29/08/2025Keep going into autumn 🍂 👖: N2N Bodywear 🩲: Box Menswear 121
Chicago Briefs @chicagobriefs.bsky.social · 14/08/2025Wearing my two favorite brands to workout in. 👖: N2N Bodywear 🩲: @petitqunderwear.bsky.social 141
Chicago Briefs @chicagobriefs.bsky.social · 13/08/2025Taking advantage of these spectacular summer sunrises 🌅 👖: Puma 🩲: N2N Bodywear 121
Chicago Briefs @chicagobriefs.bsky.social · 04/08/2025Monday morning 🤦🏻 👖: GX3 Underwear 🩲: Propaganda Tokyo 031
Chicago Briefs @chicagobriefs.bsky.social · 25/07/2025Would you still consider them shorts if you can see through them 👀? 👖: @GX 🩲: @petitqunderwear.bsky.social 131
Chicago Briefs @chicagobriefs.bsky.social · 23/07/2025Stopped at the end of my run to drop trou and take some lakeside sunrise photos 🩲: @cocksox.bsky.social 161
Chicago Briefs @chicagobriefs.bsky.social · 23/07/2025Chicago can be a beautiful city when the light is just right. 👖: N2N 🩲: Mundo Unico 051
Chicago Briefs @chicagobriefs.bsky.social · 21/07/2025First time using a singlet at the gym. Not a bad experience. 👖: N2N Bodywear 🩲: @petitqunderwear.bsky.social 082
Chicago Briefs @chicagobriefs.bsky.social · 18/07/2025Cool and dry morning along the Chicago riverwalk. 👖: N2N bodywear 🩲: Dietz 111
Chicago Briefs @chicagobriefs.bsky.social · 16/07/2025The colors were so striking at sunset this morning. 👖: Compressionz 🩲: @2xist2.bsky.social 111
Chicago Briefs @chicagobriefs.bsky.social · 29/06/2025The sky was pretty this morning, so I took some on/off photos. Enjoy! 👖: Doreanse 🩲: BoxMenswear 072
Chicago Briefs @chicagobriefs.bsky.social · 23/06/2025Definitely too hot for briefs 🥵 👖: Nike 🩲: Cocksox 161
Chicago Briefs @chicagobriefs.bsky.social · 16/06/2025Pretty sure that these aren’t meant to be used as outerwear but still….😜 👖: @GX3_UNDERWEAR 🩲: @JackAdamsUSA 151
Chicago Briefs @chicagobriefs.bsky.social · 09/06/2025Starting a new work week in these stripey thongs. 👖: GX3 🩲: @petitqunderwear.bsky.social 161
Chicago Briefs @chicagobriefs.bsky.social · 04/06/2025Great morning run 🏃 views 👖: Compressionz 🩲: N2N Bodywear 180
Chicago Briefs @chicagobriefs.bsky.social · 15/05/2025Chicago skyline views 👖: Compressionz 🩲: C-in2 031
Chicago Briefs @chicagobriefs.bsky.social · 10/05/2025I wanna soak up the sun 🌞 👖: Compressionz 🩲: N2N 052
Chicago Briefs @chicagobriefs.bsky.social · 05/05/2025Mondays, right? 👖: BCNU / Jack Adams 🩲: CIN2 132
Chicago Briefs @chicagobriefs.bsky.social · 28/04/2025Starting off a new work week 💪🏻 👖: N2N Bodywear 🩲: @aussiebum.bsky.social 152
Chicago Briefs @chicagobriefs.bsky.social · 21/04/2025Back in the CHI and hitting the gym. 👖: Nike 🩲: Todd Sanfield Collection 041
Chicago Briefs @chicagobriefs.bsky.social · 15/04/2025Early morning indoor run 🏃 👖: UnderArmour 🩲: @petitqunderwear.bsky.social 162
Chicago Briefs @chicagobriefs.bsky.social · 13/04/2025Warmish (for Chicago) weather this morning = 10 km run 👖: Compressionz 🩲: @aussiebum.bsky.social 021
Chicago Briefs @chicagobriefs.bsky.social · 09/04/2025Still cold but it’s undeniably worth it to run outdoors when you are greeted by the sun climbing the sky. 👖: Compressionz 🩲: Todd Sanfield 010
Chicago Briefs @chicagobriefs.bsky.social · 06/04/2025Yeah it’s still cold in Chicago but not cold enough to prevent me from enjoying the sun rising over Lake Michigan during my Sunday morning 10 km run☀️ 👖: Compressionz 🩲: Playboy 031
